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Total Synthesis of (+)‐Alsmaphorazine C and Formal Synthesis of (+)‐Strictamine: A Photo‐Fries Approach
Author(s) -
Gao Beiling,
Yao Fengjie,
Zhang Zhaodong,
Ding Hanfeng
Publication year - 2021
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202101752
Subject(s) - formal synthesis , imine , divergent synthesis , total synthesis , monoterpene , combinatorial chemistry , chemistry , continuous flow , indole test , stereochemistry , organic chemistry , catalysis , biochemical engineering , engineering
Abstract A bioinspired photo‐Fries/imine capture cascade reaction was developed in continuous‐flow mode, which facilitated the rapid construction of a series of diversely functionalized 2,7‐heterocycle‐fused tetrahydrocarbazoles, the ubiquitous core structures embedded in strychnos and akuammiline‐type monoterpene indole alkaloids. The synthetic utility of this novel method has been preliminarily explored by the first total synthesis of (+)‐alsmaphorazine C and formal synthesis of (+)‐strictamine in a concise and efficient manner.